Modified horner–emmons reaction of polymeric phosphonates: Versatile synthesis of pendant stilbene‐containing polymers

Abstract

SYNOPSISPoly[styrene-co-(diethyl vinylbenzylphosphonate)] and poly[methylmethacrylate-co-(diethyl vinylbenzylphosphonate)] were prepared and used in modified Horner-Emmons reactions to synthesize polymers with covalently attached stilbene groups. This versatile new method allowed for the preparation of polymers with either electron-donor (OCH3, CH3) or electron-acceptor (Br, NOz) substituents on the stilbene aromatic ring. The resulting polymers were characterized by 'H NMR, FT-IR, UV-visible, DSC, and size exclusion chromatography. Efficient transformation of polymeric pbosphonates to the polymeric stilbene derivatives was realized. Size exclusion chromatographic analyses demonstrated that the reaction conditions have no deleterious effect on the molecular weight distribution of the various polymers that were prepared. Photochromic behavior was demonstrated for one of the derivatives. 0

Two‐Photon 3D Optical Data Storage via Fluorescence Modulation of an Efficient Fluorene Dye by a Photochromic Diarylethene

“…Spectroscopic grade hexane (Alfa Aesar), THF, and ethylacetate (Acros) were used as solvents. Preparation of poly[methylmethacrylate-co-(diethyl vinyl benzyl phosphonate)] was described previously [8]. Absorption spectra were recorded with an UV-vis Agilent 8453 spectrophotometer.…”

“…Diarylethene 1 and fluorene 2 were dispersed into poly[methylmethacrylate-co-(diethylvinylbenzylphosphonate)] (PMMA-co-VBP) [8] to make the photochromic polymeric storage medium. This polymer was chosen due to its excellent solubility in acetonitrile and its ability to solubilize diarylethene 1 and fluorene 2 at high concentrations without aggregation.…”

Two-photon Absorbing Photonic Materials: From Fundamentals to Applications

“…Stable uniform films were obtained by mixing closed form diarylethene 54 and fluorene 17 with poly[methylmethacrylate-co-(diethylvinylbenzylphosphonate)] (PMMA-co-VBP) [93]. The deep red films coated on glass slides were approximately 40 µm.…”

Electronic energy transfer in pendant MEH-PPV polymers

“…Synthesis of these polymers, with a known confined MEH-PPV conjugation length, should enable control over spectral tunability and allow a closer investigation of interchromophore interactions including energy transfer processes. While there have been a few reports of the synthesis of specific confined conjugation length polymers, [16][17][18][19] our strategy is to sequentially control conjugation length and study the effects on the polymer photophysics.…”